U.S. patent application number 13/901983 was filed with the patent office on 2013-11-28 for composition and method for treating textiles.
This patent application is currently assigned to Momentive Performance Materials Inc.. The applicant listed for this patent is Momentive Performance Materials Inc.. Invention is credited to Wanchao Jiang, Mark LEATHERMAN, Yong LONG, Shingo TABEI, Renwei WANG.
Application Number | 20130316606 13/901983 |
Document ID | / |
Family ID | 48577931 |
Filed Date | 2013-11-28 |
United States Patent
Application |
20130316606 |
Kind Code |
A1 |
Jiang; Wanchao ; et
al. |
November 28, 2013 |
COMPOSITION AND METHOD FOR TREATING TEXTILES
Abstract
A curable composition useful for treating textiles to impart
thereto upon the curing of one or more textile use-enhancing
characteristics includes a first macromonomer (i) which is a
polysiloxane possessing two or more terminal functional groups
selected from the group consisting of hydroxyl, alkoxy and
combinations thereof, a second macromonomer (ii) which is a
polysiloxane containing two or more hydrosilyl (.ident.C--SiH)
groups, catalyst (iii) and, optionally, one more additional
component(s) (iv) such as surfactant(s), water, etc.
Inventors: |
Jiang; Wanchao; (Shanghai,
CN) ; TABEI; Shingo; (Shanghai, CN) ;
LEATHERMAN; Mark; (Stamford, CT) ; WANG; Renwei;
(Shanghai, CN) ; LONG; Yong; (Shanghai,
CN) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Momentive Performance Materials Inc. |
Waterford |
NY |
US |
|
|
Assignee: |
Momentive Performance Materials
Inc.
Waterford
NY
|
Family ID: |
48577931 |
Appl. No.: |
13/901983 |
Filed: |
May 24, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
61651047 |
May 24, 2012 |
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Current U.S.
Class: |
442/157 ;
252/8.85; 252/8.86; 427/389.9; 427/393.2 |
Current CPC
Class: |
C08L 83/06 20130101;
D06M 2200/45 20130101; C08L 83/08 20130101; D06M 2101/12 20130101;
C08G 77/16 20130101; C08G 77/18 20130101; Y10T 442/2803 20150401;
C08G 77/12 20130101; C08G 77/26 20130101; C08L 83/04 20130101; C08L
83/04 20130101; C08G 77/14 20130101; D06M 2200/50 20130101; C08L
83/06 20130101; D06M 15/6436 20130101; D06M 2200/35 20130101; C08L
2205/02 20130101; D06M 15/65 20130101; D06M 15/3568 20130101; C08L
83/08 20130101 |
Class at
Publication: |
442/157 ;
252/8.86; 252/8.85; 427/389.9; 427/393.2 |
International
Class: |
D06M 15/356 20060101
D06M015/356 |
Claims
1. A curable composition comprising: at least one macromonomer (i)
which is a polysiloxane of general formula (I):
M.sup.A.sub.aD.sup.B.sub.bD.sup.C.sub.cT.sup.D.sub.dT.sup.E.sub.eM.sup.A.-
sub.a (I) wherein M.sup.A is
(OR.sup.1).sub.y(R.sup.2).sub.3-ySiO.sub.1/2; D.sup.B is
R.sup.3.sub.2SiO.sub.2/2; D.sup.C is R.sup.4R.sup.5SiO.sub.2/2;
T.sup.D is R.sup.6SiO.sub.3/2; and, T.sup.E is R.sup.7SiO.sub.3/2;
in which R.sup.1, each instance, is independently hydrogen or a
monovalent hydrocarbon group of from 1 to 22 carbon atoms; R.sup.2,
R.sup.3, R.sup.4 and R.sup.6, each instance, is independently a
monovalent hydrocarbon or alkoxy group of from 1 to 22 carbon
atoms; R.sup.5 and R.sup.7, each instance, is independently a
monovalent hydrocarbon group of from 1 to 22 carbon atoms and
substituted with at least one amino and/or oxirane group; and,
1.ltoreq.a.ltoreq.19, 1.ltoreq.b.ltoreq.9999, 1.ltoreq.c.ltoreq.19,
0.ltoreq.d.ltoreq.9, 0.ltoreq.e.ltoreq.9 and 0.ltoreq.y.ltoreq.3;
at least one macromonomer (ii) which is an oligomer or polymer
containing at least two silylhydride functional groups per
molecule; at least one catalyst (iii) for the copolymerization
reaction of macromonomer(s) (i) and (ii); and, optionally, at least
one additional component (iv) selected from the group consisting of
surfactant(s) and aqueous surfactant(s).
2. The curable composition of claim 1 wherein each R.sup.1 is
hydrogen.
3. The curable composition of claim 1 wherein in general formula
(I) each R.sup.1 independently is a monovalent hydrocarbon group of
from 1 to 6 carbon atoms.
4. The curable composition of claim 1 wherein
silylhydride-containing macromonomer(s) (ii) are of the general
formula (II):
M.sub.fM.sup.H.sub.gD.sub.hD.sup.H.sub.iT.sub.jT.sup.H.sub.kQ.sub.l
(II) wherein M is R.sup.8R.sup.9R.sup.10SiO.sub.1/2; M.sup.H is
R.sup.11R.sup.12R.sup.13SiO.sub.1/2; D is
R.sup.14R.sup.15SiO.sub.2/2; D.sup.H is
R.sup.16R.sup.17SiO.sub.2/2; T is R.sup.18SiO.sub.3/2; T.sup.H/is
R.sup.19SiO.sub.3/2; Q is SiO.sub.4/2; in which R.sup.8, R.sup.9,
R.sup.10, R.sup.14, R.sup.15 and R.sup.18, each instance,
independently is alkyl, aryl or aralkyl of up to 22 carbon atoms;
R.sup.11, R.sup.16 and R.sup.19 each is hydrogen; R.sup.12,
R.sup.13 and R.sup.17, each instance, independently is hydrogen or
alkyl, aryl or aralkyl of up to 22 carbon atoms; and, f, g, h, i,
j, k and l are each integers wherein: f, g, j, k and l are each
greater than or equal to 0 and less than or equal to 50,
0.ltoreq.h.ltoreq.2000, 0.ltoreq.i.ltoreq.200, and provided that
(f+g).ltoreq.(2+3i+3k+4l) and 1.5.ltoreq.(g+i+k).ltoreq.200.
5. The curable composition of claim 4 wherein at least one monomer
is an MD-type of polysiloxane having one or more M and/or M.sup.H
groups in combination with one or more D and/or D.sup.H groups,
wherein M represents Si(CH.sub.3).sub.3O--, M.sup.H represents
HSi(CH.sub.3).sub.2O--, D represents --Si(CH.sub.3).sub.2O--, and
D.sup.H represents --Si(H)(CH.sub.3)O--.
6. The curable composition of claim 1 wherein catalyst (iii) is at
least one member of the group consisting of metallic fatty acid
salt, amine, quaternary ammonium hydroxide and Lewis acid.
7. The curable composition of claim 1 substantially devoid of
organic solvent(s).
8. A method for treating a textile to impart at least one
property-enhancing characteristic thereto comprising: a) applying
to a textile an amount of curable composition which after
undergoing curing provides at least one cured resin which is
effective to impart at least one textile property enhancing
characteristic thereto, the curable composition comprising: at
least one monomer (i) which is a polysiloxane of general formula
(I):
M.sup.A.sub.aD.sup.B.sub.bD.sup.C.sub.cT.sup.D.sub.dT.sup.E.sub.eM.sup.A.-
sub.a (I) wherein M.sup.A is
(OR.sup.1).sub.y(R.sup.2).sub.3-ySiO.sub.1/2; D.sup.B is
R.sup.3.sub.2SiO.sub.2/2; D.sup.C is R.sup.4R.sup.5SiO.sub.2/2;
T.sup.D is R.sup.6SiO.sub.3/2; and, T.sup.E is R.sup.7SiO.sub.3/2;
in which R.sup.1, each instance, is independently hydrogen or a
monovalent hydrocarbon group of from 1 to 22 carbon atoms; R.sup.2,
R.sup.3, R.sup.4 and R.sup.6, each instance, is independently a
monovalent hydrocarbon or alkoxy group of from 1 to 22 carbon
atoms; R.sup.5 and R.sup.7, each instance, is independently a
monovalent hydrocarbon group of from 1 to 22 carbon atoms and
substituted with at least one amino and/or oxirane group; and,
1.ltoreq.a.ltoreq.19, 1.ltoreq.b.ltoreq.9999, 1.ltoreq.c.ltoreq.19,
0.ltoreq.d.ltoreq.9, 0.ltoreq.e.ltoreq.9 and 0.ltoreq.y.ltoreq.3;
at least one macromonomer (ii) which is an oligomer or polymer
containing at least two silylhydride functional groups per
molecule; at least one catalyst (iii) for the copolymerization
reaction of macromonomer(s) (i) and (ii); and, optionally, at least
one additional component (iv) selected from the group consisting of
surfactant(s) and aqueous surfactant(s); and, b) subjecting the
curable composition to curing conditions to produce a cured resin
composition of macromonomer(s) (i) and (ii) and impart to the
textile at least one property-enhancing characteristic.
9. The method of claim 8 wherein the textile is in whole or in part
a cellulosic textile to which the cured resin composition imparts a
wrinkling resistant characteristic or the textile is in whole or in
part a woolen textile to which the cured resin composition imparts
an anti-pilling characteristic.
10. The method of claim 8 wherein in general formula (I), each
R.sup.1 is hydrogen.
11. The method of claim 8 wherein in general formula (I), each
R.sup.1 is a monovalent hydrocarbon group of from 1 to 6 carbon
atoms.
12. The method of claim 8 wherein silylhydride-containing
macromonomer(s) (ii) are of the general formula (II):
M.sub.fM.sup.H.sub.gD.sub.hD.sup.H.sub.iT.sub.jT.sup.H.sub.kQ.sub.l
(II) wherein M is R.sup.8R.sup.9R.sup.10SiO.sub.1/2; M.sup.H is
R.sup.11R.sup.12R.sup.13SiO.sub.1/2; D is
R.sup.14R.sup.15SiO.sub.2/2; D.sup.H is
R.sup.16R.sup.17SiO.sub.2/2; T is R.sup.18SiO.sub.3/2; T.sup.H/is
R.sup.19SiO.sub.3/2; Q is SiO.sub.4/2; in which R.sup.8, R.sup.9,
R.sup.10, R.sup.14, R.sup.15 and R.sup.18, each instance,
independently is alkyl, aryl or aralkyl of up to 22 carbon atoms;
R.sup.11, R.sup.16 and R.sup.19 each is hydrogen; R.sup.12,
R.sup.13 and R.sup.17, each instance, independently is hydrogen or
alkyl, aryl or aralkyl of up to 22 carbon atoms; and, f, g, h, i,
j, k and l are each integers wherein: f, g, j, k and l are each
greater than or equal to 0 and less than or equal to 50,
0.ltoreq.h.ltoreq.2000, 0.ltoreq.i.ltoreq.200, and provided that
(f+g).ltoreq.(2+3i+3k+4l) and 1.5.ltoreq.(g+i+k).ltoreq.200.
13. The method of claim 12 wherein at least one monomer is an
MD-type of polysiloxane having one or more M and/or M.sup.H groups
in combination with one or more D and/or D.sup.H groups, wherein M
represents Si(CH.sub.3).sub.3O--, M.sup.H represents
HSi(CH.sub.3).sub.2O--, D represents Si(CH.sub.3).sub.2O--, and
D.sup.H represents --Si(H)(CH.sub.3)O--.
14. The method of claim 8 wherein catalyst (iii) is at least one
member of the group consisting of metallic fatty acid salt, amine,
quaternary ammonium hydroxide and Lewis acid.
15. The method of claim 8 wherein the curable composition is
substantially devoid of organic solvent(s).
16. The cured resin composition obtained from the curing of the
curable composition of claim 1.
17. The cured resin composition obtained from the curing of the
curable composition of claim 4.
18. A textile having applied thereto the curable composition of
claim 1.
19. A textile having applied thereto the curable composition of
claim 4.
20. A textile having applied thereto the curable composition of
claim 7.
21. The textile of claim 18 which in whole or in part is a
cellulosic textile or a woolen textile.
22. The textile of claim 19 which in whole or in part is a
cellulosic textile or a woolen textile.
23. The textile of claim 20 which in whole or in part is a
cellulosic textile or a woolen textile.
24. A textile having applied thereto the cured resin composition
resulting from the curing of the curable composition of claim
1.
25. A textile having applied thereto the cured resin composition
resulting from the curing of the curable composition of claim
4.
26. The textile of claim 24 which in whole or in part is a
cellulosic textile or a woolen textile.
27. The textile of claim 25 which in whole or in part is a
cellulosic textile or a woolen textile.
28. The textile of claim 26 wherein the textile is in whole or in
part a cellulosic textile to which the cured resin composition
imparts a wrinkling resistant characteristic or the textile is in
whole or in part a woolen textile to which the cured resin
composition imparts an anti-pilling characteristic.
29. The textile of claim 27 wherein the textile is in whole or in
part a cellulosic textile to which the cured resin composition
imparts a wrinkling resistant characteristic thereto or the textile
is in whole or in part a woolen textile to which the cured resin
composition imparts an anti-pilling characteristic.
Description
FIELD OF THE INVENTION
[0001] The present invention relates to a composition and method
for treating textiles to impart one or more desirable properties
thereto such as shrink resistance, wrinkle resistance, durable
press, anti-pilling (in the case of woolen fabrics and wool
blends), smoothness and elastic hand feel.
BACKGROUND OF THE INVENTION
[0002] The frequent use and care of textile articles such as
linens, garments and fabrics of all kinds, etc., can lead to their
wrinkling. In particular, the wear and care (such as home
laundering) of garments may result in their wrinkling. A variety of
methods for imparting wrinkle resistance to textiles are known
including physical and chemical approaches. A widely employed
chemical-based procedure employs formaldehyde derivatives such as
dimethyloldihydroxyethyleneurea (DMDHEU) as a textile-treating
agent. Formaldehyde derivatives have long been used for this
purpose due to their effectiveness and relatively low cost.
[0003] However, formaldehyde derivatives are subject to a number of
drawbacks including reduction in fabric strength, formaldehyde
release and harsh hand feel.
[0004] Approaches to avoiding or lessening the formaldehyde release
problem have included reacting water-soluble alcohols with
hydroxymethylated organic carbamates and using crosslinked
polymaleates as formaldehyde-free durable press finishes. In order
to reduce or inhibit reduction in textile strength and improve hand
feel, polysiloxane has been employed together with known and
conventional wrinkle reducing agents as cellulosic textile-treating
agents.
SUMMARY OF THE INVENTION
[0005] The present invention fulfills the need for a composition
and method for imparting at least one textile property-enhancing
characteristic thereto, e.g., shrink resistance, wrinkle
resistance, durable press, anti-pilling (in the case of woolen
fabrics and wool blends), smoothness and/or elastic desirable hand
feel, unaccompanied by the emission of harsh chemical odors and/or
excessive or accelerated loss of strength of the treated
textiles.
[0006] In accordance with the present invention, there is provided
a cured resin composition for treating a textile to impart at least
one textile property-enhancing characteristic thereto
comprising:
[0007] at least one macromonomer (i) which is a polysiloxane of
general formula (I):
M.sup.A.sub.aD.sup.B.sub.bD.sup.C.sub.cT.sup.D.sub.dT.sup.E.sub.eM.sup.A-
.sub.a (I) [0008] wherein [0009] M.sup.A is
(OR.sup.1).sub.y(R.sup.2).sub.3-ySiO.sub.1/2; [0010] D.sup.B is
R.sup.3.sub.2SiO.sub.2/2; [0011] D.sup.C is
R.sup.4R.sup.5SiO.sub.2/2; [0012] T.sup.D is R.sup.6SiO.sub.3/2;
and, [0013] T.sup.E is R.sup.7SiO.sub.3/2; [0014] in which [0015]
R.sup.1, each instance, is independently hydrogen or a monovalent
hydrocarbon group of from 1 to 22 carbon atoms; [0016] R.sup.2,
R.sup.3, R.sup.4 and R.sup.6, each instance, is independently a
monovalent hydrocarbon or alkoxy group of from 1 to 22 carbon
atoms; [0017] R.sup.5 and R.sup.7, each instance, is independently
a monovalent hydrocarbon group of from 1 to 22 carbon atoms and
substituted with at least one amino and/or oxirane group; and,
[0018] 1.ltoreq.a.ltoreq.19, 1.ltoreq.b.ltoreq.9999,
1.ltoreq.c.ltoreq.19, 0.ltoreq.d.ltoreq.9, 0.ltoreq.e.ltoreq.9 and
0.ltoreq.y.ltoreq.3; [0019] at least one macromonomer (ii) which is
an oligomer or polymer containing at least two silylhydride
(.ident.C--SiH) functional groups per molecule; [0020] at least one
catalyst (iii) for the curing reaction of macromonomers (i) and
(ii); and, [0021] optionally, at least one additional component
(iv) selected from the group consisting of surfactant(s) and
aqueous surfactant(s).
[0022] Further in accordance with the present invention, there is
provided a method for treating a textile to impart at least one
property-enhancing characteristic thereto comprising:
[0023] a) applying to a textile an amount of curable composition
which after undergoing curing provides at least one cured resin
composition which is effective to impart at least one textile
property enhancing characteristic thereto, the curable composition
comprising:
[0024] at least one macromonomer (i) which is a polysiloxane of
general formula (I):
M.sup.A.sub.aD.sup.B.sub.bD.sup.C.sub.cT.sup.D.sub.dT.sup.E.sub.eM.sup.A-
.sub.a (I) [0025] wherein [0026] M.sup.A is
(OR.sup.1).sub.y(R.sup.2).sub.3-ySiO.sub.1/2; [0027] D.sup.B is
R.sup.3.sub.2SiO.sub.2/2; [0028] D.sup.C is
R.sup.4R.sup.5SiO.sub.2/2; [0029] T.sup.D is R.sup.6SiO.sub.3/2;
and, [0030] T.sup.E is R.sup.7SiO.sub.3/2; [0031] in which [0032]
R.sup.1, each instance, is independently hydrogen or a monovalent
hydrocarbon group of from 1 to 22 carbon atoms; [0033] R.sup.2,
R.sup.3, R.sup.4 and R.sup.6, each instance, is independently a
monovalent hydrocarbon or alkoxy group of from 1 to 22 carbon
atoms; [0034] R.sup.5 and R.sup.7, each instance, is independently
a monovalent hydrocarbon group of from 1 to 22 carbon atoms and
substituted with at least one amino and/or oxirane group; and,
[0035] 1.ltoreq.a.ltoreq.19, 1.ltoreq.b.ltoreq.9999,
1.ltoreq.c.ltoreq.19, 0.ltoreq.d.ltoreq.9, 0.ltoreq.e.ltoreq.9 and
0.ltoreq.y.ltoreq.3; [0036] at least one macromonomer (ii) which is
an oligomer or polymer containing at least two silylhydride
(.ident.C--SiH) functional groups per molecule; [0037] at least one
catalyst (iii) for the curing reaction of macromonomers (i) and
(ii); and, [0038] optionally, at least one additional component
(iv) selected from the group consisting of surfactant(s) and
aqueous surfactant(s); and,
[0039] b) subjecting the curable composition to curing conditions
to produce a cured resin composition of macromonomer(s) (i) and
(ii) and impart to the textile at least one property-enhancing
characteristic.
DESCRIPTION OF THE INVENTION
[0040] As used herein, approximating language may be applied to
modify a representation that may vary without resulting in a change
in the basic function to which it is related. Accordingly, a
description or value modified by a term or terms, such as
"substantially" may not to be limited to the precise description or
value specified, in some cases.
[0041] All ranges in the specifications and claims are inclusive of
the endpoints and independently combinable. Numerical values in the
specifications and claims are not limited to the specified values
and may include values that differ from the specified value.
[0042] Numerical values are understood to be sufficiently imprecise
to include values approximating the stated values, allowing for
experimental errors due to the measurement techniques known in the
art and/or the precision of an instrument used to determine the
values.
[0043] It will be understood that any numerical range recited
herein is intended to include all sub-ranges within that range and
any combination of the various endpoints of such ranges or
subranges.
[0044] The term "textile" as used herein shall be understood to
include blended and non-blended textile fibers and strands,
knitted, woven, non-woven or otherwise constructed fabrics, and
finished and semi-finished textile articles and subunits thereof
such as garments and garment sections, etc.
[0045] The curing of macromonomers (i) and (ii) involves the
reaction of hydroxyl and/or alkoxyl groups present in each M.sup.A
moiety of macromonomer(s) (i) with silyl hydride (.ident.C--SiH)
groups present in macromonomer(s) (ii). When the reactive groups in
moieties M.sup.A are hydroxyl (i.e., the case where each R.sup.1
group is hydrogen and each R.sup.2 group, where present, is
monovalent hydrocarbon), the curing reaction results in the
condensation of macromonomers (i) and (ii) to form cured resin
composition possessing --SiO-- linkages accompanied by the release
of hydrogen; when the reactive groups in moieties M.sup.A are
alkoxy (i.e., the case where each R.sup.1 group is a monovalent
hydrocarbon and each R.sup.2 group, where present, is alkoxy), the
curing reaction will also result in condensation of macromonomers
(i) and (ii) to form cured resin composition possessing --SiO--
linkages but with the splitting out of hydrocarbon R.sup.1H wherein
R.sup.1 is a monovalent hydrocarbon group as defined above. When
macromonomer (i) possesses both hydroxyl and alkoxy functionality,
in addition to the desired cured resin composition, hydrogen and
hydrocarbon R.sup.1H will both be formed as reaction
by-products.
[0046] The present invention also includes the cured resin
composition resulting from the curing reaction of macromonomers (i)
and (ii) contained in the aforedescribed curable resin composition,
textile treated with the curable resin composition and textile
containing cured resin composition resulting from the curing
reaction of macromonomers (i) and (ii).
[0047] Since cured resin composition derived from the curing
reaction of macromonomers (i) and (ii) contains no
formaldehyde-releasing component(s), a textile containing the cured
resin composition is not subject to the release of disagreeable
odors as are textiles treated with known and conventional
formaldehyde derivative-based textile treating agents such as those
referred to above. Use of the textile-treating composition of the
invention permits one to dispense with the use of such formaldehyde
derivatives entirely or to reduce their presence to such a level
that formaldehyde release is no longer a significant problem. In
general, it is preferred that the curable textile-treating
composition of this invention and the resulting cured resin
composition contain no, or at most 20 weight percent, formaldehyde
derivative(s) as auxiliary anti-wrinkling additive(s).
[0048] The curable composition herein, the resulting cured resin
composition and textile treating method of this invention are
particularly advantageous for providing shrink resistant and
wrinkle resistant textiles and textiles exhibiting favorable
strength retention and hand characteristics. In the case of
textiles based on wool and wool blends, the cured resin composition
of the invention advantageously imparts an effective anti-pilling
characteristic thereto.
[0049] (a) Hydroxyl and/or Alkoxy Group-Terminated Macromonomer
(i)
[0050] The curable composition of the present invention includes at
least one macromonomer (i) which is a polysiloxane of general
formula (I):
M.sup.A.sub.aD.sup.B.sub.bD.sup.C.sub.cT.sup.D.sub.dT.sup.E.sub.eM.sup.A-
.sub.a (I)
[0051] wherein
[0052] M.sup.A is (OR.sup.1).sub.y(R.sup.2).sub.3-ySiO.sub.1/2;
[0053] D.sup.B is R.sup.3.sub.2SiO.sub.2/2;
[0054] D.sup.C is R.sup.4R.sup.5SiO.sub.2/2;
[0055] T.sup.D is R.sup.6SiO.sub.3/2; and,
[0056] T.sup.E is R.sup.7SiO.sub.3/2;
[0057] in which
[0058] R.sup.1, each instance, is independently hydrogen or a
monovalent hydrocarbon group of from 1 to 22 carbon atoms;
[0059] R.sup.2, R.sup.3, R.sup.4 and R.sup.6, each instance, is
independently a monovalent hydrocarbon or alkoxy group of from 1 to
22 carbon atoms;
[0060] R.sup.5 and R.sup.7, each instance, is independently a
monovalent hydrocarbon group of from 1 to 22 carbon atoms and
substituted with at least one amino and/or oxirane group; and,
[0061] 1.ltoreq.a.ltoreq.19, 1.ltoreq.b.ltoreq.9999,
1.ltoreq.c.ltoreq.19, 0.ltoreq.d.ltoreq.9, 0.ltoreq.e.ltoreq.9 and
0.ltoreq.y.ltoreq.3;
[0062] In monomer(s) (i), each R.sup.1 independently is hydrogen or
a monovalent hydrocarbon group preferably having from 1 to 6 carbon
atoms and more preferably from 1 to 4 carbon atoms.
[0063] Each R.sup.2, R.sup.3, R.sup.4 and R.sup.6 independently is
preferably a monovalent hydrocarbon or alkoxy group of from 1 to 6
carbon atoms, e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy and
isomers thereof, and more preferably, from 1 to 4 carbon atoms,
e.g., methoxy, ethoxy, propoxy, butoxy, and isomers thereof.
[0064] Each R.sup.5 and R.sup.7 group independently is preferably a
monovalent linear or branched hydrocarbon group of from 2 to 20
carbon atoms, and more preferably, from 2 to 10 carbon atoms.
[0065] Values for a, b, c, d and are: 1.ltoreq.a.ltoreq.19,
1.ltoreq.b.ltoreq.9999, 1.ltoreq.c.ltoreq.19, 0.ltoreq.d.ltoreq.9,
0.ltoreq.e.ltoreq.9 and 0.ltoreq.y.ltoreq.3. Preferably the values
are 2.ltoreq.a.ltoreq.9, 25.ltoreq.b.ltoreq.999,
1.ltoreq.c.ltoreq.9, 0.ltoreq.d.ltoreq.5, 0.ltoreq.e.ltoreq.5 and
0.ltoreq.y.ltoreq.2 and more preferably, 2.ltoreq.a.ltoreq.5,
100.ltoreq.b.ltoreq.999, 1.ltoreq.c.ltoreq.7, 0.ltoreq.d.ltoreq.3,
0.ltoreq.e.ltoreq.3 and 0.ltoreq.y.ltoreq.1.
[0066] Monomer(s) (i) preferably have a number average molecular
weight ranging from 100 to 200,000 and preferably from 1000 to
100,000.
[0067] The macromonomer (i) component(s) of the curable composition
can be obtained by combining at least one cyclic and/or linear
siloxane, at least one alkoxy-terminated functional silane,
optional catalyst, optional surfactant(s) and water to provide a
reaction mixture and heating the mixture to a temperature and for a
period of time sufficient to achieve substantially complete
conversion of the siloxane and alkoxy silane reactants to
monomer(s) (i). Thus, e.g., a reaction mixture can be prepared by
combining at least one silanol group-containing cyclic siloxane
such as hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane or
decamethylcyctopentasiloxane (commonly referred to, respectively,
as D.sub.3, D.sub.4 and D.sub.5, available from Momentive
Performance Materials Inc.) and/or at least one silanol-containing
linear siloxane with at least one aminoalkoxysilane, e.g.,
gamma-aminopropyl trimethoxy silane, aminopropyl triisopropoxy
silane, and the like, optional catalyst(s), e.g., a strong base
such as sodium hydroxide, potassium hydroxide, ammonium hydroxide,
and the like, optional surfactant(s), e.g., anionic surfactant(s)
such as polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl
ethers, and the like, anionic surfactant(s) such as sodium lauryl
sulfate, sodium dodecybenzene sulfonate, and the like, cationic
surfactant(s) such as quarternary ammonium salts, and the like,
combinations thereof, and water for emulsification of the
macromonomer (i) reaction product(s) and heating the reaction
mixture to a suitable reaction temperature, e.g., from 90 to
140.degree. C., for a suitable period of time, e.g., from 5 to 10
hours, to achieve substantially complete conversation of the
reactants to macromonomer(s) (i).
[0068] For further details of the foregoing method for making
macromonomers (i), reference may be made to Published U.S. Patent
Application No. 2012/0114928, the entire contents of which are
incorporated by reference herein.
[0069] Several macromonomers (i) are commercially available, in
particular, YMR7212, LE-467, Magmasoft SL-501, SM 2725 and SM2068A,
all from Momentive Performance Materials Inc.
[0070] (b) Silylhydride-Containing Macromonomers (II)
[0071] The curable resin-forming composition of the invention also
includes at least one macromonomer (ii) which is an oligomer or
polymer containing at least two silylhydride (.ident.C--SiH)
functional groups per molecule.
[0072] In one embodiment of the invention, silylhydride
(.ident.C--SiH)-containing macromonomers (ii) can be selected from
among those of general formula (II):
M.sub.fM.sup.H.sub.gD.sub.hD.sup.H.sub.iT.sub.jT.sup.H.sub.kQ.sub.l
(II)
[0073] wherein [0074] M is R.sup.8R.sup.9R.sup.10SiO.sub.1/2;
[0075] M.sup.H is R.sup.11R.sup.12R.sup.13SiO.sub.1/2; [0076] D is
R.sup.14R.sup.15SiO.sub.2/2; [0077] D.sup.H is
R.sup.16R.sup.17SiO.sub.2/2; [0078] T is R.sup.18SiO.sub.3/2;
[0079] T.sup.H/is R.sup.19SiO.sub.3/2; [0080] Q is SiO.sub.4/2;
[0081] in which [0082] R.sup.8, R.sup.9, R.sup.10, R.sup.14,
R.sup.15 and R.sup.18, each instance, independently is alkyl, aryl
or aralkyl of up to 22 carbon atoms; [0083] R.sup.11, R.sup.16 and
R.sup.19 each is hydrogen; [0084] R.sup.12, R.sup.13 and R.sup.17,
each instance, independently is hydrogen or alkyl, aryl or aralkyl
of up to 22 carbon atoms; and, [0085] f, g, h, i, j, k and l are
each integers wherein: [0086] f, g, j, k and l are each greater
than or equal to 0 and less than or equal to 50, [0087]
0.ltoreq.h.ltoreq.2000, 0.ltoreq.i.ltoreq.200, and provided that
(f+g).ltoreq.(2+3i+3k+4l) and 1.5.ltoreq.(g+i+k).ltoreq.200.
[0088] In a preferred embodiment, R.sup.8, R.sup.9, R.sup.10,
R.sup.11, R.sup.12, R.sup.14, R.sup.15 and R.sup.18, each instance,
independently is alkyl of from 1 to 6 carbon atoms, and still more
preferably methyl or ethyl, R.sup.13 is hydrogen and
4.ltoreq.i.ltoreq.30; 1.ltoreq.n.ltoreq.15 and h, j, k, l and m are
each 0. In an alternative preferred embodiment, R.sup.14, R.sup.15
and R.sup.17, each instance, independently is alkyl of from 1 to 12
carbon atoms, R.sup.13 and R.sup.16 are each hydrogen and h+i=2,
0.ltoreq.j.ltoreq.100, 2.ltoreq.k.ltoreq.100 and l, m and n are
each 0.
[0089] Some examples of silylhydride-containing macromonomer(s)
(ii) include any of the linear, branched and/or crosslinked
polymers having any two or more of a combination of M, D, T, and Q
groups, as defined above, and having at least two silylhydride
functional groups.
[0090] In a particular embodiment, macromonomer(s) (ii) of general
formula (II) is an MD-type of polysiloxane having one or more M
and/or M.sup.H groups in combination with one or more D and/or
D.sup.H groups, wherein M represents Si(CH.sub.3).sub.3O--, M.sup.H
represents HSi(CH.sub.3).sub.2O--, D represents
Si(CH.sub.3).sub.2O--, and D.sup.H/represents Si(H)(CH.sub.3)O--.
Some examples of suitable MD-type polysiloxanes for monomer (ii)
include the M.sup.HD.sub.nM.sup.H, M.sup.HD.sup.H.sub.nM,
M.sup.HD.sup.H.sub.nD.sub.mM, M.sup.HD.sub.nM.sup.H,
M.sup.HD.sup.H.sub.nD.sub.mM.sup.H, MD.sup.H.sub.nD.sub.mM classes
of MD-type polysiloxanes, and combinations thereof, wherein m and n
each represent an integer at least 1 to 500. The D.sup.H groups can
also be randomly incorporated (i.e., not as a block) among the D
groups. For example, M.sup.HD.sup.H.sub.nD.sub.mM can represent a
polymer wherein n represents 5-20 and m represents 50-1500, and
wherein the 5-20 D.sup.H groups are randomly incorporated among the
50-1500 D groups.
[0091] In other embodiments, M.sup.H and D.sup.H groups can
independently have a higher number of silylhydride functional
groups such as, for example, H.sub.2Si(CH.sub.3)O-- and
H.sub.3SiO-- groups for M.sup.H or --Si(H).sub.2O-- for
D.sup.H.
[0092] Macromonomer(s) (ii) preferably have a number average
molecular weight of from 200 to 30,000 and preferably from 500 to
20,000.
[0093] The macromonomer (ii) component(s) of the curable
composition can be obtained by carrying out the cohydrolysis
reaction of two or more different alkylhalosilanes, e.g.,
SiH(CH.sub.3)Cl.sub.2 with one or more of Si(CH.sub.3).sub.3Cl,
SiH(CH.sub.3).sub.2Cl, Si(CH.sub.3).sub.2Cl.sub.2 and
Si(CH.sub.3)Cl.sub.3, in the presence of water at, e.g., from 5 to
30.degree. C. for from 5 to 30 hours.
[0094] Two commercially available macromonomers (ii) are TSF 484
and SS 4300C, both from Momentive Performance Materials Inc.
[0095] (c) Catalyst (iii)
[0096] The curable textile-treating composition of the invention
includes at least one catalyst (iii) effective for catalyzing the
curing reaction of macromonomers (i) and (ii) therein, to produce
cured resin composition in which the macromonomer units are linked
together through SiO-- linkages.
[0097] Catalyst (iii) may be selected from the metallic fatty acid
salts, amines, quaternary ammonium hydroxides, Lewis acids, and the
like. Examples of useful metallic fatty acid salts include
dibutyltin diacetate, dibutyltin dioctoate, dibutyltin dilaurate,
dibutyltin dioleate, dibutyltin distearate, tributyltin acetate,
tributyltin octoate, tributyltin laurate, dioctyltin diacetate,
dioctyltin dilaurate, diethyltin dioleate and monomethyltin
dioleate which have hydrocarbon groups directly bonded to metallic
atoms, and zinc octenoate, iron octenoate and tin octenoate which
do not have hydrocarbon groups directly bonded to metallic atoms.
Examples of useful amines include organic amines such as
monomethylamine, dimethylamine, monoethylamine, diethylamine,
ethylenediamine and hexamethylenetetramine, amino group-containing
silane compounds such as .alpha.-aminopropyltriethoxysilane and
their salts. Examples of useful quaternary ammonium hydroxides
include tetramethylammonium hydroxide, dimethylbenzyl ammonium
hydroxide and their salts. Examples of useful Lewis acids include
FeCl.sub.3, AlCl.sub.3, ZnCl.sub.2, ZnBr.sub.2, as well as those
Lewis acids having greater solubility in siloxane media disclosed
in U.S. Pat. No. 7,064,173, the entire contents of which are
incorporated by reference herein.
[0098] (iv) Optional Components
[0099] Since mixtures of macromonomers (i) and (ii) even in the
absence of catalyst (iii) can undergo a significant level of curing
over relatively lengthy periods of time, say, over three months to
two years and longer, it is desirable to keep them apart until just
before they are needed for a textile coating operation. As a
practical matter, then, it is preferred to provide the curable
composition of this invention as two, or even three, isolated
units, i.e., macromonomer(s) (i) as one unit, macromonomer(s) (ii)
as the second unit with catalyst(s) (iii) and optional component(s)
(iv) added to unit (i) and/or unit (ii) or, preferably, provided as
its own separate third unit. Shortly prior to use in a
textile-treating operation, predetermined amounts of each unit are
combined employing known and conventional mixing equipment and
procedures to provide the curable textile-treating composition of
the invention.
[0100] In a preferred embodiment of the invention, the individual
units of macromonomers (i) and (ii), and if maintained separately
from the macromonomers, catalyst(s) (iii), are provided as aqueous
emulsions employing suitable surfactant(s) as emulsifier(s).
Following the curing reaction of macromonomers (i) and (ii) to
yield cured resin composition, the cured resin will be dispersed
within the surfactant(s) contained in the curable reaction medium.
The use of surfactant(s) therefore allows both the curable
composition and the subsequently cured resin to be applied to the
textile as a water-based system, one containing no or at most only
a minor amount by weight, e.g., not exceeding 20 weight percent of
the total curable composition, of one or a mixture of organic
solvents. In a more preferred embodiment, the curable
textile-treating composition of the invention is substantially
devoid of organic solvent(s) and thus can be regarded as an
essentially organic solvent-free system.
[0101] Useful surfactants for the emulsification of the
textile-treating composition herein can be selected from known and
conventional nonionic, cationic or anionic surfactants.
[0102] Useful nonionic surfactants include those having hydrophilic
lipophilic balance (HLB) between 5 and 25. Some useful nonionic
surfactants of this category are polyoxyalkylene alkyl ethers,
polyoxyalkylene sorbitan esters, polyoxyalkylene esters and
polyoxyalkylene alkylphenyl ethers. Some specific examples of
primary surfactant are Brij 35, Brig 35L, Brij 58, Brij 78, Brij
98, Brij 700, and Brij 721, all products of Croda.
[0103] Cationic surfactants useful for emulsifying the components
of the curable composition of this invention include compounds
containing quaternary ammonium hydrophilic moieties in the molecule
which are positively charged such as quaternary ammonium salts or
bases represented by R.sup.3R.sup.4R.sup.5R.sup.6N.sup.+X.sup.-
where R.sup.3 to R.sup.6 are alkyl groups containing from 10 to 30
carbon atoms, or alkyl groups derived from tallow, coconut oil or
soy and X is hydroxide or halogen, e.g., chlorine or bromine.
Dialkyl dimethyl ammonium salts which can be used are represented
by R.sup.7R.sup.8N.sup.+(CH.sub.3).sub.2X.sup.- where R.sup.7 and
R.sup.8 are alkyl groups containing from 10 to 30 carbon atoms or
alkyl groups derived from tallow, coconut oil or soy and X is
hydroxide or halogen. Monoalkyl trimethyl ammonium salts which can
be used herein are represented by
R.sup.9N.sup.+(CH.sub.3).sub.3X.sup.- where R.sub.9 is an alkyl
group containing from 10 to 30 carbon atoms or an alkyl group
derived from tallow, coconut oil or soy and X is halogen.
Representative quaternary ammonium salts and hydroxides are
dodecyltrimethyl ammonium chloride/lauryltrimethyl ammonium
chloride (LTAC), cetyltrimethyl ammonium chloride (CTAC),
didodecyldimethyl ammonium bromide, dihexadecyldimethyl
ammoniumchloride, dihexadecyldimethyl ammonium bromide,
dioctadecyldimethyl ammonium chloride, dieicosyldimethyl ammonium
chloride, didocosyldimethyl ammonium chloride, dicoconutdimethyl
ammonium chloride, ditallowedimethyl ammonium chloride,
ditallowedimethylammonium bromide and cetyltrimethyl ammonium
hydroxide. These and other quaternary ammonium salts are
commercially available under names such as Adogen, Arquad, Tomah
and Variquat.
[0104] Anionic surfactants useful for emulsifying the components of
the curable composition of this invention include sulfonic acids
and their salt derivatives. Some representative examples of useful
anionic surfactants are alkali metal sulfosuccinates; sulfonated
glyceryl esters of fatty acids useful such as sulfonated
monoglycerides of coconut oil acids; salts of sulfonated monovalent
alcohol esters such as sodium oleyl isethionate; amides of amino
sulfonic acids such as the sodium salt of oleyl methyl tauride;
sulfonated products of fatty acidnitriles such as palmitonitrile
sulfonate; sulfonated aromatic hydrocarbons such as sodium
alpha-naphthalene monosulfonate; condensation products of
naphthalene sulfonic acids with formaldehyde; sodium octahydro
anthracene sulfonate; alkali metal alkylsulfates; ether sulfates
having alkyl groups of eight or more carbon atoms such as sodium
lauryl ether sulfate; and alkylaryl sulfonates having one or more
alkyl groups of eight or more carbon atoms such as hexadecylbenzene
sulfonic acid and C.sub.20 alkylbenzene sulfonic acid.
[0105] Additional optional components of the curable composition of
the invention include minor amounts of one or more organic solvents
such as monohydric and polyhydric alcohols (when aqueous emulsions
of curable and cured compositions are employed as described above),
pH buffering agents such as strong or weak acids, e.g., HCl,
H.sub.2SO.sub.4, phosphoric, benzoic or citric acid (the pH of the
compositions are preferably less than 5.0), rewetting agents,
viscosity modifiers such as electrolytes, for example, calcium
chloride, anti-gelling agents, fragrances, fragrance carriers,
fluorescers, colorants, hydrotropes, antifoaming agents,
anti-redeposition agents, enzymes, optical brightening agents,
opacifiers, stabilizers such as guar gum and polyethylene glycol,
anti-shrinking agents, fabric crisping agents, anti-spotting
agents, soil-release agents, germicides, fungicides, biocides,
anti-oxidants, anti-corrosion agents, preservatives, pigments,
dyes, bleaches and bleach precursors, drape imparting agents,
antistatic agents, fillers, thickeners, ironing aids, and the
like.
[0106] These and other optional components, if utilized, can be
incorporated in the copolymer-forming composition in known and
conventional amounts. The optional components can be incorporated
in one or more of the aforementioned individual reaction component
units to be later combined to provide the copolymer-forming
composition herein (with due attention to storage stability
concerns) or they can be added individually, in various
sub-combinations or all at once when several optional components
are utilized during or after the combining and mixing operation
resulting in the fully formulated copolymer-forming
composition.
[0107] The amount of water used in the preparation of aqueous
emulsions of macromonomers (i) and (ii) should be adequate to
provide either an oil-in-water emulsion or a water-in-oil emulsion
of good stability. In most cases, the amount of water can be in the
range of from about 20 parts by weight (pbw) to about 2000 pbw,
preferably from about 100 pbw to about 500 pbw, per 100 pbw of the
total amount of monomers (i) and (ii).
[0108] Fully formulated curable compositions of this invention can
be prepared by merely mixing and agitating macromonomers (i) and
(ii), catalyst(s) (iii) and optional additional component(s) (iv)
with a stirrer, e.g., a homogenizer. The components of the
copolymer-forming composition can be introduced together into a
vessel in a specific amount or as a pre-mixture of macromonomers
(i) and (ii), catalyst(s) (iii) and optional component(s) (iv)
followed by the addition of water. In this manner an aqueous
emulsion of curable composition of the oil-in-water or water-in-oil
type is readily and conveniently obtained to provide the cellulosic
textile-treating composition herein. The length of time for
agitation depends upon the balance of the interfacial properties
between the components of the curable composition including any
optional surfactant(s) (iv) and water.
[0109] (e) Procedures for Applying Curable Textile-Treating
Composition to Textiles
[0110] Table 1 below sets forth suitable broad and preferred ranges
for each of monomers (i) and (ii), catalyst(s) (iii) and optional
components such as surfactants (iv), water, etc., for the
copolymer-forming composition of the invention.
TABLE-US-00001 TABLE 1 Weight Ranges of Components of the Curable
Textile-Treating Composition As a Percent of the Total Composition
Broad Range Preferred Range Required Components macromonomer(s) (i)
60-97 75-90.0 macromonomer(s) (ii) 3-35 5-20 catalyst(s) (iii)
0.1-5 0.5-1 Optional Components (iv) (when utilized) surfactant(s)
1-80 2-10 Water 35-90 45-70 Other(s) 0.25-5 0.5-2
[0111] Examples of textiles for treatment herein include nylon
(polyamides), polyester, wool, cotton, flax, hemp, jute and ramie,
and the like, including blends of any of the foregoing with one or
more other natural or synthetic fibers. Thus, e.g., cotton and wool
can be blended with fibers derived from polyesters, polyamides
(e.g., nylons), acrylics (e.g., polyacrylonitrile), polyolefins,
polyvinyl chloride, and polyvinylidene chloride. Preferably, the
textiles based on blends of fibers include at least 35 to 40
percent by weight, and most preferably at least 50 to 60 percent by
weight, of cotton or other cellulosic fiber.
[0112] The curable cellulosic textile treating composition of the
present invention, advantageously containing one or more
surfactants (iv) as described above, can be diluted with water to a
desired active level and applied to a fiber or textile by any
suitable means such as spraying, dipping, padding, kiss roll, and
the like. Removal of any treating composition can be achieved by
using a mangle, centrifugal separator, or the like, to control the
amount of liquid absorbed by the textile. Drying can be effected
with or without heat. Depending upon the particular textile being
treated, when drying is performed by application of heat, the
drying temperature can generally range from 70.degree. to
130.degree. C. and its duration from 1 to 30 minutes. After removal
of any excess emulsion, subsequent heating to complete curing is
usually required. Effective curing temperatures generally range
from 130.degree. C. to 200.degree. C. for periods of from 1 to 30
minutes. Following curing, the cured resin(s) impart one or more
advantageous properties to the treated textile, e.g., shrink
resistance, wrinkle resistance and/or desirable hand feel
characteristics.
[0113] The amount of aqueous emulsion of curable composition that a
treated textile absorbs will generally range from 0.1 to about 5
weight percent based on the total weight of macromonomers (i) and
(ii). It may be desirable to prepare emulsified reaction component
units having higher macromonomer contents in order to reduce
shipping and/or handling costs and then to dilute the emulsions
with water immediately prior to use. The macromonomer contents of
the curable composition herein can range from 10 to 80 weight
percent, preferably from 20 to 40 weight percent, based on the
total weight of the composition.
[0114] The following examples illustrate the preparation of several
curable textile-treating compositions and their use in treating
textiles, specifically, cotton woven (Table 2) and wool knits
(Table 3), to impart, respectively, a wrinkling resistance property
and an anti-pilling property thereto in accordance with the
invention.
[0115] Examples 1 to 3 illustrate the preparation of three
different macromonomers (i), Examples 4 to 6 illustrate the
preparation of three different macromonomers (ii) and Examples 7-9
illustrate the preparation of three different catalysts (iii). In
these examples, all indicated percents and parts are by weight.
Example 1
[0116] 0.4% of a C-15 secondary alcohol with 15 moles ethylene
oxide (tergitol 15-s-15, Dow Chemical), 4% hexadecyl trimethyl
ammonium chloride (cationic surfactant), 4% polyoxyethylene alkyl
ether (nonionic surfactant; Emulsogen 1135S-70, Kao Chem.) and
59.6% water were charged to a 4-neck 250 ml reactor and mixed for
10 min under low agitation (200 rpm) with a radical flow sweep
blade. Thereafter, 30% of octamethylcyclotetrasiloxane (D.sub.4)
was charged to the vessel and mixed for 50 min under high agitation
(600 rpm). The pre-emulsion was homogenized with the first pressure
50 kg and the second pressure 500 kg to provide an emulsion.
Thereafter catalyst (2.0% of an aqueous solution of 10% KOH in
water) was charged into the vessel. The vessel was then slowly
heated to 80.degree. C. for 5 hours, and then the temperature was
decreased to 45.degree. C. and maintained for 12 hours. Thereafter,
0.2% of acetic acid was charged to neutralize the solution.
Example 2
[0117] 16 parts of a silanol terminated polysiloxane (viscosity:
40,000 cps) was mixed with 8 parts TERGITOL TMN-6 and then 76 parts
water was added slowly at 800-1000 rpm to form a homogeneous
mixture.
Example 3
[0118] 2.4% of a C-15 secondary alcohol with 15 moles ethylene
oxide (tergitol 15-s-15, Dow Chemical), 4% hexadecyl trimethyl
ammonium chloride (cationic surfactant) and 56.4% water were
charged to a 4-neck 250 ml reactor and mixed for 10 min. under low
agitation (200 rpm) with a radical flow sweep blade. Thereafter,
35% of octamethylcyclotetrasiloxane (D.sub.4) was charged to the
vessel and mixed for 50 min under high agitation (600 rpm). The
pre-emulsion was homogenized with the first pressure 50 kg and the
second pressure 500 kg to give an emulsion. Thereafter catalyst
(2.0% of an aqueous solution of 10% KOH in water) was charged into
the vessel. The vessel was then slowly heated to 80.degree. C. for
5 hours, and then the temperature was decreased to 45.degree. C.
and maintained for 12 hours. Thereafter, 0.2% of acetic acid was
charged to neutralize the solution.
Example 4
[0119] 2% of a C-13 isotridecanol with 5 moles ethylene oxide, 2%
of a C-13 isotridecanol with 7 moles ethylene oxide, 30% of
hydrogen polysiloxane (TSF 484, 1.6% hydrogen content, Momentive
Performance Materials), 0.5% of acetic acid and 65.5% of water were
charged to a 4-neck 1 liter reactor and mixed for 10 min. And then
the pre-emulsion was homogenized with the first pressure 50 kg and
the second pressure 500 kg to provide a stable emulsion.
Example 5
[0120] 3% of a C-13 isotridecanol with 6 moles ethylene oxide, 3%
of a C-13 isotridecanol with 9 moles ethylene oxide, 35% of
hydrogen polysiloxane (TSF 484, 1.6% hydrogen content, Momentive
Performance Materials), 0.5% of acetic acid and 58.5% of water were
charged to a 4-neck 1 liter reactor and mixed for 10 min. And then
the pre-emulsion was homogenized with the first pressure 50 kg and
the second pressure 500 kg to provide a stable emulsion.
Example 6
[0121] 1% of a C-13 isotridecanol with 6 moles ethylene oxide, 3%
of a C-13 isotridecanol with 12 moles ethylene oxide, 35% of
hydrogen polysiloxane (TSF 484, 1.6% hydrogen content, Momentive
Performance Materials), 0.5% of acetic acid and 60.5% of water were
charged to a 4-neck 1 liter reactor and mixed for 10 min. And then
the pre-emulsion was homogenized with the first pressure 50 kg and
the second pressure 500 kg to provide a stable emulsion.
Example 7
[0122] 80% of Dibutyltin Dilaurate was blended with 20% C-13
isotridecanol with 5 moles ethylene oxide (Multiso 13-50, available
from Sasol Chemical).
Example 8
[0123] 50% of diethyltin dioleate was blended with 50% C-13
isotridecanol with 6 moles ethylene oxide (Multiso 13-60, available
from Sasol Chemical).
Example 9
[0124] 50% of tributyltin laurate was blended with 50% C-13
isotridecanol with 9 moles ethylene oxide (Multiso 13-90, available
from Sasol Chemical),
[0125] The following treatment conditions were employed: drying at
130.degree. C. for 2 minutes and curing at 160.degree. C. for 1
minute. The treated textiles were specimens of 100% cotton woven
(40*40, 186 g/m.sup.2) (Table 2) and 100% wool knits (Table 3).
[0126] In the experimental data reported in Table 2 below, hand
feel was evaluated by a panel of five experienced individuals, hand
feel being rated on a scale of 1 to 5 with 5=very soft and slick
and 1=harsh. Recovery Angle, a measure of wrinkle resistance for
woven fabrics, was measured substantially in accordance with AATCC
Test Method 66-2003 and Tear Strength was measured by
Falling-Pendulum (Elmendorf-type) Apparatus in accordance with
ASTMD 1429-09.
[0127] In the experimental data reported in Table 3, hand feel was
evaluated by a panel of five as in the case of Table 2 and the
anti-pilling rating was measured substantially in accordance with
ASTMD Test Method 3512.
[0128] The results of the aforedescribed tests were as follows:
TABLE-US-00002 TABLE 2 Test Results for Treated Cotton Woven Curing
Recovery Macromonomer Macromonomer Catalyst Angle (.degree., Tear
Strength (i) (ii) (iii) Hand Feel weft + warp) (N, weft + warp)
Control -- -- -- Harsh 90 35 Dosage 100 of 10 of 1 of Smooth 200 56
(g/l) Example 1 Example 4 Example 7 and bouncy 200 of 20 of 2 of
Smooth 220 67 Example 2 Example 5 Example 8 and bouncy 100 of 30 of
2 of Smooth 230 62 Example 3 Example 6 Example 9 and bouncy
[0129] As the test data in Table 2 show, compared with the control
specimens of cotton woven to which no wrinkle resistant additive
was applied, the specimens of cotton woven dosed with curable
compositions formulated with macromonomers (i) and (ii) and
catalyst (iii) in accordance with the invention (Examples 1-9) and,
following curing, containing the resulting cured resin composition,
exhibited significantly improved hand feel, Recovery Angle and Tear
Strength.
TABLE-US-00003 TABLE 3 Test Results for Treated Wool Knits
Macromonomer Macromonomer Curing Anti-pilling (i) (ii) Catalyst
(iii) Hand Feel rating Control -- -- -- Harsh 2 Dosage 100 of 10 of
Example 4 1 of Example 7 Smooth and 3 (g/l) Example 1 bouncy 200 of
20 of Example 5 2 of Example 8 Smooth and 3 Example 2 bouncy 100 of
30 of Example 6 2 of Example 9 Smooth and 3 Example 3 bouncy
[0130] As shown in the experimental data set forth in Table 3, the
control specimens of wool knits to which no anti-pilling additive
was applied exhibited harsh hand feel and a relatively low
anti-pilling rating compared with the specimens of wool knits
treated in accordance with the invention which exhibited both
significantly improved hand feel and anti-pilling rating.
[0131] While the invention has been described with reference to a
preferable embodiment, those skilled in the art will understand
that various changes may be made and equivalents may be substituted
for elements thereof without departing from the scope of the
invention. It is intended that the invention not be limited to the
particular embodiment disclosed as the best mode for carrying out
this invention, but that the invention will include all embodiments
falling within the scope of the appended claims. All citations
referred herein are expressly incorporated herein by reference.
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